DE1263777B - Verfahren zur Herstellung von Hexamethylendiamin durch katalytische Hydrierung von Adipinsaeurenitril - Google Patents
Verfahren zur Herstellung von Hexamethylendiamin durch katalytische Hydrierung von AdipinsaeurenitrilInfo
- Publication number
- DE1263777B DE1263777B DEM60522A DEM0060522A DE1263777B DE 1263777 B DE1263777 B DE 1263777B DE M60522 A DEM60522 A DE M60522A DE M0060522 A DEM0060522 A DE M0060522A DE 1263777 B DE1263777 B DE 1263777B
- Authority
- DE
- Germany
- Prior art keywords
- magnetic
- catalyst
- hydrogenation
- hexamethylenediamine
- pellets
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 title claims description 28
- BTGRAWJCKBQKAO-UHFFFAOYSA-N adiponitrile Chemical compound N#CCCCCC#N BTGRAWJCKBQKAO-UHFFFAOYSA-N 0.000 title claims description 20
- 238000000034 method Methods 0.000 title claims description 19
- 238000009903 catalytic hydrogenation reaction Methods 0.000 title claims description 5
- 238000004519 manufacturing process Methods 0.000 title description 4
- 230000005291 magnetic effect Effects 0.000 claims description 109
- 239000003054 catalyst Substances 0.000 claims description 83
- 238000005984 hydrogenation reaction Methods 0.000 claims description 25
- 229910017052 cobalt Inorganic materials 0.000 claims description 20
- 239000010941 cobalt Substances 0.000 claims description 20
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 20
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 16
- 229910052739 hydrogen Inorganic materials 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 11
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 10
- 229910021529 ammonia Inorganic materials 0.000 claims description 8
- 238000000926 separation method Methods 0.000 claims description 7
- 229910052759 nickel Inorganic materials 0.000 claims description 5
- 238000002360 preparation method Methods 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 1
- 239000008188 pellet Substances 0.000 description 28
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- 238000005245 sintering Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 10
- 238000003786 synthesis reaction Methods 0.000 description 6
- 230000015572 biosynthetic process Effects 0.000 description 5
- 229910000428 cobalt oxide Inorganic materials 0.000 description 5
- IVMYJDGYRUAWML-UHFFFAOYSA-N cobalt(ii) oxide Chemical compound [Co]=O IVMYJDGYRUAWML-UHFFFAOYSA-N 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000006148 magnetic separator Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 150000007513 acids Chemical class 0.000 description 3
- 239000000314 lubricant Substances 0.000 description 3
- WQEPLUUGTLDZJY-UHFFFAOYSA-N pentadecanoic acid Chemical compound CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000010924 continuous production Methods 0.000 description 2
- 230000003247 decreasing effect Effects 0.000 description 2
- 230000005294 ferromagnetic effect Effects 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- 238000007885 magnetic separation Methods 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- SZHOJFHSIKHZHA-UHFFFAOYSA-N tridecanoic acid Chemical compound CCCCCCCCCCCCC(O)=O SZHOJFHSIKHZHA-UHFFFAOYSA-N 0.000 description 2
- PVNIQBQSYATKKL-UHFFFAOYSA-N tripalmitin Chemical compound CCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCC PVNIQBQSYATKKL-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- DSEKYWAQQVUQTP-UHFFFAOYSA-N Cerin Natural products CC12CCC3(C)C4CC(C)(C)CCC4(C)CCC3(C)C2CCC2(C)C1CC(O)C(=O)C2C DSEKYWAQQVUQTP-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- 241001043922 Pensacola Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 235000021355 Stearic acid Nutrition 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 238000010923 batch production Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920005646 polycarboxylate Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C209/00—Preparation of compounds containing amino groups bound to a carbon skeleton
- C07C209/44—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers
- C07C209/48—Preparation of compounds containing amino groups bound to a carbon skeleton by reduction of carboxylic acids or esters thereof in presence of ammonia or amines, or by reduction of nitriles, carboxylic acid amides, imines or imino-ethers by reduction of nitriles
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J23/00—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00
- B01J23/70—Catalysts comprising metals or metal oxides or hydroxides, not provided for in group B01J21/00 of the iron group metals or copper
- B01J23/74—Iron group metals
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J37/00—Processes, in general, for preparing catalysts; Processes, in general, for activation of catalysts
- B01J37/34—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation
- B01J37/341—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation
- B01J37/342—Irradiation by, or application of, electric, magnetic or wave energy, e.g. ultrasonic waves ; Ionic sputtering; Flame or plasma spraying; Particle radiation making use of electric or magnetic fields, wave energy or particle radiation of electric, magnetic or electromagnetic fields, e.g. for magnetic separation
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B35/00—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products
- C04B35/01—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics
- C04B35/26—Shaped ceramic products characterised by their composition; Ceramics compositions; Processing powders of inorganic compounds preparatory to the manufacturing of ceramic products based on oxide ceramics based on ferrites
- C04B35/2666—Other ferrites containing nickel, copper or cobalt
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Physics & Mathematics (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Ceramic Engineering (AREA)
- Plasma & Fusion (AREA)
- Toxicology (AREA)
- Structural Engineering (AREA)
- Manufacturing & Machinery (AREA)
- Electromagnetism (AREA)
- Optics & Photonics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US270161A US3272867A (en) | 1963-04-03 | 1963-04-03 | Process for catalytic hydrogenation of adiponitrile |
| US270160A US3272866A (en) | 1963-04-03 | 1963-04-03 | Process for catalytic hydrogenation of adiponitrile |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1263777B true DE1263777B (de) | 1968-03-21 |
Family
ID=26954104
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DEM60522A Pending DE1263777B (de) | 1963-04-03 | 1964-04-02 | Verfahren zur Herstellung von Hexamethylendiamin durch katalytische Hydrierung von Adipinsaeurenitril |
Country Status (7)
| Country | Link |
|---|---|
| US (2) | US3272867A (enrdf_load_stackoverflow) |
| BE (1) | BE645928A (enrdf_load_stackoverflow) |
| CH (1) | CH435218A (enrdf_load_stackoverflow) |
| DE (1) | DE1263777B (enrdf_load_stackoverflow) |
| GB (1) | GB1050519A (enrdf_load_stackoverflow) |
| LU (1) | LU45747A1 (enrdf_load_stackoverflow) |
| NL (1) | NL6403584A (enrdf_load_stackoverflow) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4388327A (en) * | 1981-10-30 | 1983-06-14 | E. I. Du Pont De Nemours & Co. | Method of increasing milk production of dairy cattle |
| US6017563A (en) * | 1997-07-25 | 2000-01-25 | Novus International, Inc. | Process for optimizing milk production |
| US8067332B2 (en) * | 2006-05-03 | 2011-11-29 | Samsung Sdi Co., Ltd. | Methanation catalyst, and carbon monoxide removing system, fuel processor, and fuel cell including the same |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US707706A (en) * | 1902-02-12 | 1902-08-26 | W F Botsford | Extension-pedal for pianos. |
| US2166150A (en) * | 1935-11-15 | 1939-07-18 | Du Pont | Catalytic hydrogenation of dinitriles to diamines |
| US2225059A (en) * | 1938-09-28 | 1940-12-17 | Du Pont | Process for catalytic hydrogenation of higher aliphatic nitriles |
| US2677668A (en) * | 1945-01-11 | 1954-05-04 | Atomic Energy Commission | Stabilization of reduced metal catalyst |
| US2707706A (en) * | 1949-12-06 | 1955-05-03 | Exxon Research Engineering Co | Method of reducing catalyst |
-
0
- GB GB1050519D patent/GB1050519A/en active Active
-
1963
- 1963-04-03 US US270161A patent/US3272867A/en not_active Expired - Lifetime
- 1963-04-03 US US270160A patent/US3272866A/en not_active Expired - Lifetime
-
1964
- 1964-03-26 LU LU45747D patent/LU45747A1/xx unknown
- 1964-03-31 BE BE645928A patent/BE645928A/xx unknown
- 1964-03-31 CH CH404564A patent/CH435218A/fr unknown
- 1964-04-02 DE DEM60522A patent/DE1263777B/de active Pending
- 1964-04-03 NL NL6403584A patent/NL6403584A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US3272867A (en) | 1966-09-13 |
| BE645928A (enrdf_load_stackoverflow) | 1964-09-30 |
| GB1050519A (enrdf_load_stackoverflow) | |
| NL6403584A (enrdf_load_stackoverflow) | 1964-10-05 |
| US3272866A (en) | 1966-09-13 |
| LU45747A1 (enrdf_load_stackoverflow) | 1964-09-26 |
| CH435218A (fr) | 1967-05-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1302398B (enrdf_load_stackoverflow) | ||
| DE2164341C3 (de) | Verfahren zur katalytischen Hydrierung von Adiponitril zu Hexamethylendiamin | |
| DE1160833B (de) | Katalysator fuer die Ammoniaksynthese | |
| EP0186885A2 (de) | Verfahren zur Aktivierung und Stabilisierung von Katalysatormassen | |
| DE1263777B (de) | Verfahren zur Herstellung von Hexamethylendiamin durch katalytische Hydrierung von Adipinsaeurenitril | |
| DE1168892B (de) | Verfahren zur Reinigung von Butin-(2)-diol-(1, 4) | |
| DE1251308B (de) | Verfahren zur Herstellung von Allylalkohol durch Umlagerung von Propylenoxyd mit Tnlithiumphosphat als Katalysator | |
| EP0802174B1 (de) | Verfahren zur Herstellung von Hydroxymethylcyclopropan | |
| DE2429293C2 (de) | Katalysator und Verfahren zur Hydrierung von Adiponitril | |
| DE69427590T2 (de) | Verfahren zur umesterung von triglyceriden | |
| DE2304269C3 (de) | Verfahren zum Stabilisieren eines aktivierten Eisen-Hydrierungskatalysators | |
| DE2057001C3 (de) | Verfahren zur Herstellung von tertiären Aminen | |
| DE2459547C2 (de) | Verfahren zur Herstellung von Hexamethylenimin | |
| DE1269113B (de) | Verfahren zur Herstellung von aktiver Tonerde in Granulatform | |
| DE3402734A1 (de) | Geformte eisenkatalysatormasse, deren herstellung und verwendung | |
| DE1150953B (de) | Verfahren zur Herstellung von Formlingen | |
| DE1816044A1 (de) | Kernbrennstoff | |
| DE1210866B (de) | Verfahren zum kontinuierlichen Abscheiden von Melamin | |
| DE2101868C3 (de) | Verfahren zur Diamantsynthese | |
| DE3210883C2 (de) | Verfahren zur Herstellung von Diarylamin-Antioxidantien in Körnerform | |
| DE1061306B (de) | Verfahren und Vorrichtung zur Kohlenoxydhydrierung unter Verwendung kupferhaltiger Eisen-Sinterkatalysatoren | |
| DE2408431C3 (de) | Verfahren zur Herstellung von Nickelkatalysatoren mit einem Siliciumdioxyd-Träger | |
| DE1959578C (de) | Verfahren zur Herstellung sulfidierter Platin-auf- Kohlenstoff-Katalysatoren | |
| DE2620096C3 (de) | Verfahren zur kontinuierlichen Herstellung von wasserfreiem Natriumdithionit | |
| AT218260B (enrdf_load_stackoverflow) |